Lambertianic acid

Lambertianic acid
Names
IUPAC name
methyl (1S,4aR,5S,8aR)-5-[2-(furan-3-yl)ethyl]-4a-methyl-6-methylidene-1,2,3,4,5,7,8,8a-octahydronaphthalene-1-carboxylate
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C20H28O3/c1-14-6-8-18-16(19(21)22-3)5-4-11-20(18,2)17(14)9-7-15-10-12-23-13-15/h10,12-13,16-18H,1,4-9,11H2,2-3H3/t16-,17-,18+,20-/m0/s1 N
    Key: XZOUFGJMCGQXNM-GNBUJSLZSA-N
  • CC12CCCC(C1CCC(=C)C2CCC3=COC=C3)C(=O)OC
Properties
C20H28O3
Molar mass 316.441 g·mol−1
Density 1.09 g/cm3
Melting point 213 °C (415 °F; 486 K)
Boiling point 428 °C (802 °F; 701 K)
insoluble
Solubility soluble in chloroform, methanol, ethyl acetate, DMSO
Hazards
Flash point 213 °C[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Lambertianic acid is a naturally occurring organic compound classified as a diterpenoid with the molecular formula C20H28O3. This is a tricyclic carboxylic acid first isolated from the oleoresin of the Lambert pine (Pinus lambertiana), from which it derives its name. The acid is a member of the abietane family of diterpenes, characterized by its aromatic C-ring.[2]

Occurrence

Lambertianic acid was first reported by Dauben and German[3] in the mid-20th century as a major acidic constituent of the oleoresin (a mixture of resin acids and terpenes) of the sugar pine (Pinus lambertiana).[4] The acid is biosynthesized in pine trees from geranylgeranyl pyrophosphate via the diterpenoid pathway and serves as a defensive compound against insects and pathogens. The compound has also been found, often in smaller quantities, in other Pinus species and some species of the Lamiaceae family.[5]

Structure

Lambertianic acid is based on the abietane carbon skeleton. Its structure consists of three fused six-membered rings (phenanthrene framework) with a carboxylic acid (–COOH) group at the C-18 position (the fourth carbon of the original abietane side chain) and three conjugated double bonds in rings B and C at the positions 8, 11, and 13. This conjugated system contributes to its reactivity and spectroscopic properties.[6] Lambertianic acid is an optical isomer of daniellic acid.[7]

Uses

Reports indicate that the acid may offer health benefits by mitigating obesity, allergies, and various cancers such as those of the breast, liver, lung, and prostate. Its anticancer effects stem from suppressing the proliferation and survival of cancer cells.[8][9]

Lambertianic acid is structurally related to several other commercially and biologically important resin acids:

References

  1. ^ "Lambertianic Acid". Retrieved 9 February 2026.
  2. ^ Terpenoids and Steroids. Chemical Society. 1975. ISBN 978-0-85186-296-5. Retrieved 9 February 2026.
  3. ^ Bulletin of the Institute for Chemical Research, Kyoto University. Institute for Chemical Research, Kyoto University. 1967. p. 242. Retrieved 9 February 2026.
  4. ^ Proceedings. 1974. p. 48. Retrieved 9 February 2026.
  5. ^ Rahman, Atta-ur (8 February 2021). Studies in Natural Products Chemistry. Elsevier. p. 237. ISBN 978-0-12-819486-7. Retrieved 9 February 2026.
  6. ^ Dauben, W. G.; German, V. F. (1 January 1966). "The structure of lamertianic acid: A new diterpenic acid". Tetrahedron. 22 (2): 679–683. doi:10.1016/0040-4020(66)80037-6. ISSN 0040-4020. Retrieved 9 February 2026.
  7. ^ Çiçek, Serhat Sezai; Wenzel-Storjohann, Arlette; Girreser, Ulrich; Tasdemir, Deniz (1 February 2020). "Biological Activities of Two Major Copaiba Diterpenoids and Their Semi-synthetic Derivatives". Revista Brasileira de Farmacognosia. 30 (1): 18–27. doi:10.1007/s43450-020-00002-y. ISSN 1981-528X. PMC 7222050. Retrieved 9 February 2026.
  8. ^ Shahinozzaman, Md; Islam, Moutushi; Basak, Bristy; Sultana, Arifa; Emran, Rashiduzzaman; Ashrafizadeh, Milad; Islam, A T M Rafiqul (1 September 2021). "A review on chemistry, source and therapeutic potential of lambertianic acid". Zeitschrift für Naturforschung C. 76 (9–10): 347–356. doi:10.1515/znc-2020-0267. ISSN 1865-7125. Retrieved 9 February 2026.
  9. ^ Cho, Chan Hee; Chae, Si Hyeon; Um, Sung Hee; Lee, Seulah; Yu, Jae Sik; Kang, Ki Sung; Kim, Ki Hyun (January 2025). "Lambertianic Acid from Platycladus orientalis Inhibits Muscle Atrophy in Dexamethasone-Induced C2C12 Muscle Atrophy Cells". Plants. 14 (9). doi:10.3390/plants14091357. ISSN 2223-7747. PMC 12073373. Retrieved 9 February 2026.
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